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For sixteen seasons, we’ve been Keeping Up With the Kardashians.
They are the family that has dominated headlines, tabloids, and conversations for over a decade, and we absolutely love it.
As reality television’s royal family, the Kardashians and Jenners have incidentally shared the most precious moments of their lives, from tragedies, pregnancies, and heartbreaks to transitions, celebrations, and love.
When Kim was unwittingly propelled into global infamy following her notorious sex tape, the dating profiles of every family member were also launched into the spotlight. Every fling, kiss, and date has for better or worse been documented
From Khloe’s cursed love life and Kourtney’s on-and-off relationship with the father of her children to Kim’s extravagant weddings, we’ve watched, celebrated, and cried at all the ups and downs.
Now, all eyes are now focused on Kylie and Kendall Jenner and they’re just as entertaining as their older sisters.
With a slew of rappers, NBA players, and superstars already under their belt, Kendall and Kylie continue to share their lives— albeit with a little more restraint. You’ve got
If you’re a Kardashian-Jenner fan, you know that their dating lives are basically pop culture history.
Ever the romantic, Kim has never given up on love despite the drama that has followed her.
Did you know that Kim Kardashian was first married in 2000? Long before finding fame on reality tv, Kim eloped with Damon Thomas, a Grammy-nominated music producer.
The marriage came to an end in 2004 after Kim cited controlling behavior on Thomas’ behalf, stating in her divorce papers that “Damon decided what we would do and when we would do it.”
Even more startling were allegations that he forced her to get plastic surgery.
He was definitely the wrong guy for Kim.
Whether you know everything or nothing about Kim, everyone remembers when she dated Ray J. He met Kim during her short stint working with his sister, R&B singer Brandy.
As far as gross behavior goes, Ray J can win an award for his after releasing a song titled, “I Hit It First” as a pointed diss towards Kim’s now-husband, Kanye West. Classy.
Following the fall out of dating Ray J, Kim dated 98 Degrees singer Nick Lachey right off the back of his very public split with Jessica Simpson.
“Let’s just say this,” he told Details Magazine, “We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside.”
He was then asked if those paparazzi shots were the stimulus to Kim’s sudden rise to fame he answered, “That’s one way to interpret it.”
Before Nick Cannon and Mariah Carey got married, he dated Kim Kardashian. From late 2006, the two cozied up together until the beginning of 2007 when everything fell apart because of that sex tape.
He also added, “If she might have been honest with me I might have tried to hold her down…She’s actually one of the nicest people you’ll ever meet. But the fact that she lied and told me that there was no tape?” That was a dealbreaker.
NFL star, Reggie Bush had a hold on Kim’s heart for a couple of years. The on-and-off couple seemed like they’d even make it work as Reggie made short cameos on Keeping Up With The Kardashians.
But, the two just couldn’t find a way to make it work, but Reggie has nothing but sweet things to say about the mogul.
In a recent interview he admitted, “she’s doing a great job creating a brand for herself, her and her family. I’m happy for ‘em … She’s very smart.”
Finding a rhythm with another NFL player, Kim snuggled up with Dallas Cowboys star, Miles Austin for a few months in 2010.
“They tried to keep it as low profile as possible when they were together,” a source told People. “It was the real deal. They were always strong, but before Kim left for Europe they decided it’s not fair that they don’t get to spend more time together and ended it.”
When Gabriel Aubry and Halle Berry’s relationship came to an end, everyone was shocked to see Aubry move on with Kim.
According to E! factors including Halle Berry’s vocal disapproval of the new relationship, in addition to the Keeping Up star’s burgeoning crush on NBA star, Kris Humphries drove them apart.
In December 2010, Kim and Kris Humphries began dating and things moved fast. Engaged in just six months, the relationship was heavily covered on Keeping Up With The Kardashians, as was their marriage ceremony.
The couple infamously filed for divorce just 72 days after tying the knot.
After meeting her as Brandy’s assistant, Kanye West became obsessed with Kim.
The two began dating following years of knowing each other in 2012, and everything came together after that.
“I just think that Kim is awesome,” he told Ellen Degeneres in an interview, and the sentiment hasn’t changed after 5 years of marriage.
The eldest Kardashian has been in a steady relationship for most of her television career, but a hot fling suggests this hot mom is ready for some fun.
Kourt and Scott Disick were already dating when the first episode of Keeping Up With The Kardashians aired, but after 9 years the two called it quits.
Scott is still an integral part of the family – and the show – with the two finding a way to expertly co-parent.
Following her breakup with Scott, Kourtney quickly began dating 26-year-old boxer and model, Younes Bendjima.
The French hunk was spotted on various yachts with the oldest Kardashian sister and the two seemed to be having a lot of fun, until Younes let all his jealousy get in the way.
After commenting on a bikini shot of Kourtney with “thats what you need to show to get likes? [sic]” the two were promptly over.
We think she’s better off!
The youngest Kardashian sister has had a hard time finding long-lasting and reciprocal love.
In 2008, Khloe dated former basketballer, Rashad McCants but things didn’t go smoothly. Promptly after being photographed together on a red carpet in Las Vegas, the two experienced a tumultuous on-screen falling out.
McCants later revealed in an interview in 2017 that he regretted the relationship because it cost him a lasting career.
“Without that situation in play I’m a $60-70 million player,” he told the Charlotte Observer. “Easily.”
Perhaps Khloe’s most substantial relationship yet, her marriage to basketballer Lamar Odom ended in a bout of tragedy.
Exploring the ups and downs of their relationship on Keeping Up With The Kardashians their relationship ended after the former Lakers’ star struggled with infidelity and drug abuse.
Splitting up in 2013, their divorce was put on hold after Odom overdosed in a brothel in Nevada but the split was finalized in 2016.
While still in the midst of getting divorced from Lamar, Khloe began dating rapper, French Montana. According to Perez Hilton, the two started cozying up despite Montana being romantically to Miami rapper Trina, who was also Khloe’s friend at the time.
“I jumped into something because I was just, like, lonely and destructive,” she said during an episode of Kourtney & Khloe Take the Hamptons. “But now I’m like, I just want to be alone.”
Following her conscious uncoupling from French Montana in December 2014, Khloe had a few flings until she began dating another basketball player, James Harden.
Harden who plays for the Houston Rockets recently opened up about the romance, saying “I [didn’t] like all the attention. I feel like it was for no reason.
I wasn’t getting anything out of it except my name out there and my face out there, and I don’t need that.” The two broke up as Khloe helped Lamar recover from his almost fatal overdose.
Khloe began dating Cavaliers’ basketballer, Tristan Thompson in 2016 after their first appeared at Flo Rida’s birthday party together.
Despite this, they remained together until this year, when news broke that Tristan had cheated on her again, but this time with Kylie’s best friend, Jordyn Woods.
Growing up in the spotlight must be hard, but Kylie landed on the one early on in life.
This Calabasas teen romance was one for the ages.
Son of Jada and Will Smith, Jaden was locked in a flirty fling with the youngest Jenner sister for a moment or so.
Jaden even attended Kim and Kanye’s wedding, wearing a white Batman suit.
“Kylie and Jaden have been hanging out lately and it made Tyga suspicious. He thought something might be going on. So that was one issue,” a source told E! News.
Kylie and Tyga’s relationship was controversial, to say the least.
The two made their relationship public when Kylie turned 18 and gifted each other expensive cars and gifts before splitting in 2016.
Following her dramatic split with Tyga, Kylie quickly bounced back with the success of her lip kits and a brief cameo in a rap music video.
She was photographed while filming the Partynextdoor video for Partynextdoor’s song “Come And See Me.” For obvious reasons, their passionate kiss began stirring a lot of headlines.
But whatever she had with the songwriter didn’t last long.
The first time the two were spotted together was in 2017 at Coachella, but since then Travis Scott and Kylie have been inseparable.
Since then, Kylie and Travis have made it work, welcoming baby Stormi into their lives and going on tour together while keeping their relationship strong. Ah, young love.
The ultra-private fashion model has had a series of quiet flirtations, but far fewer confirmed romances.
Former One Direction member, Harry Styles has been famously private with his dating life, but in 2013 rumors began swirling that he was dating Kendall Jenner.
After sharing a dinner at celebrity hotspot, Craig’s in West Hollywood, the two began being spotted in various vacation spots.
Khloe even confirmed the two were in fact dating, but as far as relationship labels go, they were a little looser than most. The two reunited briefly at this year’s Met Gala.
While Kendall has always remained tight-lipped about her relationships, when she began dating rapper A$AP Rocky, the model appeared to enjoy the public attention. Attending the Met Gala together, the cute couple looked stunning together.
“It’s the real deal,” a source told Us Weekly, but despite this, they didn’t last very long.
Dating for just six months, Kendall’s relationship with basketball player Blake Griffin was filled with drama and lots of courtside appearances.
After getting caught up in legal troubles with the mother of his child, Brynn Cameron, it seemed that Kendall wasn’t ready for the long-haul and called it quits before anything got too serious.
Australian basketball player, Ben Simmons began dating Kendall in 2018 after the two were spotted canoodling in Beverley
Hills. While Simmons was hot off his last relationship, with R&B songstress Tinashe, it didn’t stop Kendall, who was unfazed by Tinashe trashing the two to the paparazzi.
We’re not sure if it was the cheating that drew the relationship to a close but with this much drama, it wasn’t destined to last.
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